Synthesis and Spectroscopic Characterization of Protic Tris(2-Hydroxyethyl)-Ammonium Ionic Liquids

Abstract

Protic ionic liquids (PILs) having tris(2-hydroxyethyl)ammonium (or triethanolammonium) as cations and methacrylate, dihydrogenborate, formate, acetate as anions have been synthesized through stoichiometric neutralization reaction. PILs have been characterized by elemental analyses, FTIR, ¹H and ¹³C NMR spectroscopic methods. The viscosity of PIL4 was measured using a cone-and-plate viscometer at ambient temperature. The viscosity value indicates that the fluidity of PIL4 is 829 cP (the water viscosity is 0.7977 cP at 30 °C). 

Keywords

• Protic ionic liquids,Triethanolammonium salts,Synthesis,Spectroscopy,Viscosity

References

1. Wasserscheid P, Keim W. Ionic liquids-new “solutions” for transition metal catalysis. Angew. Chem. Int. Ed. 2000;39:3772-89.
2. Chhotaray PK, Gardas RL. Thermophysical properties of ammonium and hydroxylammonium protic ionic liquids. J. Chem. Thermodynamics 2014;72:117-2
3. Marcinkowski Ł, Pena-Pereira F, Kloskowski A, Namiesnik J. Opportunities and shortcomings of ionic liquids in single-drop microextraction. Trends in Analyt. Chem. 2015;72:153-68.
4. Oliveria MVS, Vidal BT, Melo CM, de Miranda RCM, Soares CMF, Coutinho JAP, Ventura SPM, Mattedi S, Lima AS. (Eco) toxicity and biodegradability of protic ionic liquids. Chemosphere 2016;147:460-6.
5. Earle MJ, Seddon KR. Ionic liquids. Green solvents for the future. Pure Appl. Chem. 2000;72:1391-98.
6. Austen CA, Ansari Y, Zhao Z. Ionic liquids: past, present and future. Faraday Discuss. 2012;154:9-27.
7. Zhao Q, Zhao G, Zhang M, Wang X, Liu W. Tribological behavior of protic ionic liquids with dodecylamine salts of dialkyldithiocarbamate as additives in lithium complex grease. Tribol. Lett. 2012;48:133-44.
8. Espinosa T, Sanes J, Jiménez A, Bermúdez M. Protic ammonium carboxylate ionic liquid lubricants of OFHC copper. Wear 2013;303:495-509.

9. Akbaş H, Okumuş A, Karadağ A, Kılıç Z, Hökelek T, Koç LY, Açık L, Aydın B, Türk M. Structural and thermal characterizations, antimicrobial and cytotoxic activities, and in vitro DNA binding of the phosphazenium salts. J. Therm. Anal. Calorim. 2016;123:1627-41.
10. Akbaş H, Karadağ A, Aydın A, Destegül A, Kılıç Z. Synthesis, structural and thermal properties of the hexapyrrolidinocyclotriphosphazenes-based protic molten salts: Antiproliferative effects against HT29, HeLa, and C6 cancer cell lines. J. Mol. Liq. 2017;230: 482-95.
11. Nakamotoa H, Watanabe M. Brønsted acid–base ionic liquids for fuel cell electrolytes. Chem. Commun. 2007;2539-41.
12. Yasuda T, Watanabe M. Protic ionic liquids: fuel cell applications. MRS Bulletin 2013;38:560-66.
13. Vogl T, Menne S, Kühnel R, Balducci A. The beneficial effect of protic ionic liquids on the lithium environment in electrolytes for battery applications. J. Mater. Chem. A 2014;2:8258-65.
14. Akbari J, Heydari A, Ma’mani L, Hosseini SH. Protic ionic liquid [TMG][Ac] as an efficient, homogeneous and recyclable catalyst for Boc protection of amines. Chimie C.R. 2010;13:544-47.
15. Xiao L, Su D, Yue C, Wu W. Protic ionic liquids: A highly efficient catalyst for synthesis of cyclic carbonate from carbon dioxide and epoxides. J. CO2 Utilization 2014;6:1-6.
16. Choi HM, Kwon I. Dissolution of zein using protic ionic liquids: N-(2-Hydroxyethyl) ammonium formate and N-(2-hydroxyethyl) ammonium acetate. Ind. Eng. Chem. Res. 2011;50:2452-54.
17. Salari H, Harifi-Mood AR, Elahifard MR, Gholami MR. Solvatochromic probes absorbance behavior in mixtures of 2-hydroxy ethylammonium formate with methanol, ethylene glycol and glycerol. J. Sol. Chem. 2010;39:1509-19.
18. Bara JE, Camper DE, Gin DL, Noble RD. Room-temperature ionic liquids and composite materials: platform technologies for CO2 capture. Acc. Chem. Res. 2010;43:152-59.
19. Yuan X, Zhang S, Liu J, Lu X. Solubilities of CO2 in hydroxyl ammonium ionic liquids at elevated pressures. Fluid Phase Equilibria 2007;257:195-200.
20. Garaev V, Kleperis J, Pavlovica S, Vaivars G. Properties of the Nafion membrane impregnated with hydroxyl ammonium based ionic liquids. IOP Conf. Ser.: Mater. Sci. Eng. 2012;38:012064.
21. Ahfad-Hosseini HR, Bagheri H, Amidi S. Ionic liquid-assisted synthesis of celexocib using tris-(2-hydroxyethyl)ammonium acetate as an efficient and reusable catalyst. IJPR 2017;16:158-64. PMCID: PMC5423243
22. Anouti M, Caillon-Caravanier M, Le Floch C, Lemordant D. Alkylammonium-based protic ionic liquids part I: preparation and physicochemical characterization. J. Phys. Chem. B 2008;112:9406-11.
23. Pinkert A, Ang KL, Marsh KN, Pang S. Density, viscosity and electrical conductivity of protic alkanolammonium ionic liquids. Phys. Chem. Chem. Phys., 2011;13:5136-43.
24. Xu Y, Yao J, Wang C, Li H. Density, viscosity, and refractive ındex properties for the binary mixtures of n-butylammonium acetate ionic liquid + alkanols at several temperatures. J. Chem. Eng. Data 2012;57:298-308.
25. Kurnia KA, Wilfred CD, Murugesan T. Thermophysical properties of hydroxyl ammonium ionic liquids. J. Chem. Thermodynamics 2009;41:517-21.
26. Karadağ A, Destegül A. N-(2-hydroxyethyl)-ethylenediamine-based ionic liquids: Synthesis, structural characterization, thermal, dielectric and catalytic properties. J. Mol. Liq. 2013;177:369-75.
27. Yuan XL, Zhang SJ, Lu XM. Hydroxyl ammonium ionic liquids: synthesis, properties, and solubility of SO2. J. Chem. Eng. Data 2007;52:596-99.
28. Gruzdev MS, Shmukler LE, Kudryakova NO, Kolker AM, Safonova LP. Synthesis and properties of triethanolamine-based salts with mineral and organic acids as protic ionic liquids. J. Mol. Liq. 2018;249:825-30.
29. Erdik E. Organik kimyada spektroskopik yöntemler (Turkish); Gazi Büro Kitabevi: Ankara, Turkey, 1993.
30. Fundamensky VS, Kochina TA, Kondratenko YA, Zolotarev AA, Vlasov YG, Ignatyev IS. Ionic liquids based on triethanolammonium salts of dicarboxylic acids (oxalic, malonic, succinic): crystal structure and cation-anion interaction. J. Mol. Liq. 2017;230:113–20.
31. Kondratenko Y, Kochina T, Fundamensky V, Ignatyev I, Panikorovskii T, Nyanikova G. Triethanolammonium salicylate-protic alkanolammonium ionic liquid. J. Mol. Liq. 2016;221:1218–24.
32. Gruzdev MS, Shmukler LE, Kudryakova NO, Kolker AM, Sergeeva YA, Safonova LP. Triethanolamine-based protic ionic liquids with various sulfonic acids: Synthesis and properties. J. Mol. Liq. 2017;242:838-44.
33. Deacon GB, Phillips RJ. Relationships between the carbon-oxygen stretching frequencies of carboxylato complexes and the type of carboxylate coordination. Coord. Chem. Rev. 1980;33:227-50.
34. Voronkov MG, Albanov AI, Aksamentova TN, Adamovich SN, Chipanina NN, Mirskov RG, Kochina TA, Vrazhnov DV, Litvinov MY. Tris(2-hydroxyethyl)ammonium salts: 2,8,9-Trihydroprotatranes. Russ. J. Gen. Chem. 2009;79:2339-46.
35. Kondratenkoa YA, Kochina TA, Fundamensky VS, Vlasov YG. Triethanolammonium salts of biologically active carboxylic acids. Russ. J. Gen. Chem. 2015;85:2710-14.
36. Gao L, Wan H, Han M, Guan G. Deep desulfurization of model oil by extraction with a low viscosity ionic liquid [BMIM]SCN. Petrol. Sci. Tech. 2014;32:1309-17.
37. DiGuilio RM, Lee RJ, Schaeffer ST, Brasher LL, Teja AS. Densities and viscosities of the ethanolamines. J. Chem. Eng. Data 1992;37:239-42.